The first total synthesis and structural determination of epi-cochlioquinone A

Seijiro Hosokawa, Kaoru Matsushita, Shinpei Tokimatsu, Tatsuya Toriumi, Yasuaki Suzuki, Kuniaki Tatsuta

    研究成果: Article

    28 引用 (Scopus)

    抄録

    The first total synthesis of epi-cochlioquinone A has been achieved in a highly convergent manner via [3+3] cycloaddition of catechol 2 and oxadecalin 3 as the key reaction. The synthesis of the catechol segment, possessing the side chain with multi stereogenic centers, features the asymmetric vinylogous Mukaiyama aldol reaction, the stereoselective conjugate addition to the nitroalkene, the stereospecific nitro-Dieckmann condensation, and the transformation of 6-nitrocyclohex-2-enone into catechol 2, using two new methodologies, such as (i) the hydrogen-transfer reaction to o-aminophenol and the subsequent auto-redox-catalysis to catechol and (ii) the direct oxidation of 6-nitrocyclohex-2-enone to o-quinone and the subsequent reduction. The oxadecalin segment was synthesized from a glycosyl cyanide by the [3+3] annulation with a ketone and an acetoacetate. These segments were connected by the [3+3] cyclization, and the resulting tetracyclic compound was subjected to a specific oxidation of the protected hydroquinone to provide epi-cochlioquinone A.

    元の言語English
    ページ(範囲)5532-5536
    ページ数5
    ジャーナルTetrahedron Letters
    51
    発行部数42
    DOI
    出版物ステータスPublished - 2010 10 20

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    Oxidation
    Cycloaddition
    Cyclization
    Cycloaddition Reaction
    Cyanides
    Ketones
    Catalysis
    Oxidation-Reduction
    Hydrogen
    Condensation
    cochlioquinone A
    catechol
    oxadecalin
    2-aminophenol
    acetoacetic acid
    hydroquinone
    3-hydroxybutanal
    benzoquinone

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    これを引用

    Hosokawa, S., Matsushita, K., Tokimatsu, S., Toriumi, T., Suzuki, Y., & Tatsuta, K. (2010). The first total synthesis and structural determination of epi-cochlioquinone A. Tetrahedron Letters, 51(42), 5532-5536. https://doi.org/10.1016/j.tetlet.2010.07.153

    The first total synthesis and structural determination of epi-cochlioquinone A. / Hosokawa, Seijiro; Matsushita, Kaoru; Tokimatsu, Shinpei; Toriumi, Tatsuya; Suzuki, Yasuaki; Tatsuta, Kuniaki.

    :: Tetrahedron Letters, 巻 51, 番号 42, 20.10.2010, p. 5532-5536.

    研究成果: Article

    Hosokawa, S, Matsushita, K, Tokimatsu, S, Toriumi, T, Suzuki, Y & Tatsuta, K 2010, 'The first total synthesis and structural determination of epi-cochlioquinone A', Tetrahedron Letters, 巻. 51, 番号 42, pp. 5532-5536. https://doi.org/10.1016/j.tetlet.2010.07.153
    Hosokawa, Seijiro ; Matsushita, Kaoru ; Tokimatsu, Shinpei ; Toriumi, Tatsuya ; Suzuki, Yasuaki ; Tatsuta, Kuniaki. / The first total synthesis and structural determination of epi-cochlioquinone A. :: Tetrahedron Letters. 2010 ; 巻 51, 番号 42. pp. 5532-5536.
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    AU - Suzuki, Yasuaki

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